| # | Artist | Songs |
|---|---|---|
| 1 | John Prine | 60 |
| 2 | Rodney Crowell | 43 |
| 3 | Lucero | 41 |
| 4 | Orville Peck | 38 |
| 5 | Wilco | 31 |
| 6 | Neko Case | 30 |
| 7 | Ryan Adams | 25 |
| 8 | Steve Earle | 23 |
| 9 | Lucinda Williams | 22 |
| 10 | Cracker | 19 |
| 11 | Old 97's | 19 |
| 12 | Jenny Lewis | 18 |
| 13 | Nick Lowe | 17 |
| 14 | Silver Jews | 15 |
| 15 | Lyle Lovett | 14 |
| 16 | Nek | 13 |
| 17 | Townes Van Zandt | 12 |
| 18 | Purple Mountains | 10 |
| 19 | Gram Parsons | 9 |
| 20 | The Flying Burrito Brothers | 9 |